CN101870681A - Bis-phenanthroimidazolyl compound and electroluminescent device using the same - Google Patents

Bis-phenanthroimidazolyl compound and electroluminescent device using the same Download PDF

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CN101870681A
CN101870681A CN201010142046A CN201010142046A CN101870681A CN 101870681 A CN101870681 A CN 101870681A CN 201010142046 A CN201010142046 A CN 201010142046A CN 201010142046 A CN201010142046 A CN 201010142046A CN 101870681 A CN101870681 A CN 101870681A
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imidazole
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郑建鸿
刘常兴
吴芳奕
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Zheng Jianhong
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Abstract

A bis-phenanthroimidazolyl compound having a following formula is disclosed. Where A1 and A2 comprise identical or different aromatic rings, A3 comprises a polyaromatic hydrocarbon or at least two aromatic groups, and each carbon in A1 to A3 and phenanthrol groups is independently substituted or non-substituted. The bis-phenanthroimidazolyl compound exhibits relatively better thermal properties with higher glass-transition temperature and efficient blue emission. The bis-phenanthroimidazolyl compound may function as a host emitter or charge-transporter. An electroluminescent device is also disclosed.

Description

Two phenanthro-imidazole-based compounds and el light emitting device thereof
Technical field
The present invention relates to a kind of pair of phenanthro-imidazole-based compounds (bis-phenanthroimidazolylcompound) and el light emitting device thereof, a kind of pair of phenanthro-imidazole-based compounds particularly is in order to as blue light main body luminescent material or electron transport material in the Organic Light Emitting Diode.
Background technology
Because (0rganic light emitting diode OLED) applies to flat-panel screens and quite has advantage Organic Light Emitting Diode, and therefore many researchers are quite interesting to OLED.Wherein to develop into commerical prod for OLED be very important for development stability and high efficiency three primary colors (red, green, blue) luminescent material and light-emitting device.An important requirement of development Organnic electroluminescent device is for development RGB (RGB) light-emitting device, to meet the demand of color plane indicating meter.
Particularly seek efficient blue light electroluminescent material, because it is for being embodied as OLED the critical elements of demonstration and lighting use.At present existing many research teams successfully prepare efficient blue light fluorophore (fluorophore) and OLED thereof.Yet, up to the present, chromaticity y coordinate (Commission Internationale Y coordinate value, (CIE y))≤0.15 efficient material is very rare.At present still lack good organic electroluminescent compounds to meet the demand.
Comprehensively above-mentioned, need the novel luminous organic compound of development at present badly, particularly blue light can be launched, and the Organnic electroluminescent device of low power consuming can be used for effectively.
Summary of the invention
The purpose of this invention is to provide a kind of pair of phenanthro-imidazole-based compounds and be used for organic electronic device, particularly in the Organic Light Emitting Diode as main body luminescent material or electron transport material.
According to an embodiment, a kind of pair of phenanthro-imidazole-based compounds comprises following chemical formula:
Wherein, A1 and A2 comprise identical or different aromatic nucleus, and A3 comprises a polycyclic aromatic hydrocarbons or at least two aromatic series bases, and each carbon atom of A1 to A3 and phenanthro-base can have or not have substituting group independently.
Wherein the substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises halogen atom, C1～C20 alkyl chain, C1～C20 oxyalkyl chain, C1～C20 alkylhalide group chain, C1～C20 halogen oxyalkyl chain, carbonyl, cyano group or nitro.
Another object of the present invention is for providing a kind of el light emitting device, and it has the ethereal blue light of lower trigger voltage and tool good color purity, to realize more excellent electric energy efficiency.In addition, even if its efficient still can maintain high level under the situation that increases brightness.
According to another embodiment, a kind of el light emitting device comprise negative electrode, anode and be arranged at negative electrode and anode between organic layer.Comprise above-mentioned two phenanthro-imidazole-based compounds in this organic layer, this pair phenanthro-imidazole-based compounds comprises following chemical formula:
Figure GSA00000056298200022
Wherein, A1 and A2 comprise identical or different aromatic nucleus, and A3 comprises a polycyclic aromatic hydrocarbons or at least two aromatic series bases, and each carbon atom of A1 to A3 and phenanthro-base can have or not have substituting group independently.
One substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises a halogen atom, one C1～C20 alkyl chain, one C1～C20 oxyalkyl chain, one C1～C20 alkylhalide group chain, one C1～C20 halogen oxyalkyl chain, a carbonyl, a cyano group or a nitro.
Wherein, A3 is selected from the group that is made up of naphthalene, anthracene, phenanthrene, (chrysene) in the wrong and pyrene.
Wherein, A1 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
Wherein, A2 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
Wherein, described organic layer is a luminescent layer, and described pair of phenanthro-imidazole-based compounds is a main body luminescent material.
Wherein, described organic layer is a luminescent layer, and described pair of phenanthro-imidazole-based compounds is an object luminescent material.
Wherein, described organic layer is an electron transfer layer, and described pair of phenanthro-imidazole-based compounds is an electron transport material.
The present invention above-mentioned and other aspect, characteristic and advantage can be understood more by the explanation of drawings and Examples.
Description of drawings
Fig. 1 is the synoptic diagram of explanation according to the synthesis mode of two phenanthro-imidazole-based compounds of one embodiment of the invention and derivative thereof.
Fig. 2 is the synoptic diagram of explanation according to the synthesis mode of two phenanthro-imidazole-based compounds of another embodiment of the present invention and derivative thereof.
Fig. 3 is that explanation is according to the energy rank of the middle material therefor of the blue light el light emitting device of one embodiment of the invention and the synoptic diagram of chemical structure.
Fig. 4 to Fig. 7 is the experimental result of graphic explanation one embodiment of the invention.
Embodiment
The invention provides a kind of two phenanthro-imidazole-based compounds of novelty, its can in order to the preparation luminescent layer, also can be as electron transfer layer.The present invention also provides a kind of electroluminescent, and (it comprises aforesaid pair of phenanthro-imidazole-based compounds, so that the characteristics of luminescence of improvement to be provided, and can simplify the structure of Organnic electroluminescent device for electroluminescent, EL) device.
Below propose to be used for electric transmission and electroluminescent pair of phenanthro-imidazole-based compounds, it has following chemical formula.
Figure GSA00000056298200041
Wherein, A1 and A2 comprise identical or different aromatic nucleus.A3 comprises a polycyclic aromatic hydrocarbons or at least two aromatic series bases.Each carbon atom of A1 to A3 and phenanthro-base can have or not have substituting group independently, and the substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises halogen atom, C1～C20 alkyl chain, C1～C20 oxyalkyl chain, C1～C20 alkylhalide group chain, C1～C20 halogen oxyalkyl chain, carbonyl, cyano group or nitro.
Among a preferred embodiment, two phenanthro-imidazole-based compounds have two aromatic series base A4 and A5, and each carbon atom of A4 and A5 all can have or not have substituting group independently.The substituting group of each carbon atom of A4 and A5 optionally comprises halogen atom, C1～C20 alkyl chain, C1～C20 oxyalkyl chain, C1～C20 alkylhalide group chain, C1～C20 halogen oxyalkyl chain, carbonyl, cyano group or nitro.Coupling position between A4 and the A5 can be normotopia (ortho-), a position (meta-) or side position (para-).
Figure GSA00000056298200051
One of them preferred embodiment of above-mentioned two phenanthro-imidazole-based compounds is as shown below.
Figure GSA00000056298200052
Wherein R can be H, OCH 3Or OCH 3In other words, A4 and A5 are benzene ring compound, and A1 and A2 are selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
Below in Fig. 1 the synthesis mode of the two phenanthro-imidazole-based compounds of explanation and derivative thereof.Below explanation is the example of the two phenanthro-imidazole-based compounds of two steps preparation.
2-(4-bromophenyl)-1-aryl-1H-phenanthro-[9,10-d] imidazoles (2-(4-bromophenyl)-1-aryl-1H-phenanthro[9,10-d] imidazole) derivative 1a-1c's is synthetic
2-(4-bromophenyl)-1-phenyl-1H-phenanthro-[9,10-d] preparation of imdazole derivatives 1a-1c is by with 9,10-phenanthrenequione (9,10-phenanthrenequinone) (2.0g, 9.6mmol), p-bromobenzaldehyde (4-bromobenzaldehyde) (1.78g, 9.6mmol), (7.4g 96.1mmol) is dissolved in Glacial acetic acid (40ml), and the 24 hours institutes that reflux in nitrogen reach for the substituent aniline of tool (11.5mmol) and ammonium acetate.After being cooled to room temperature, reactant being poured among the methanol solution, and stirred.Isolated solid is filtered, with methanol cleaning and dry, to obtain the product of high yield.Below provide productive rate relevant optical data.
2-(4-bromophenyl)-1-phenyl-1H-phenanthro-[9,10-d] imdazole derivatives (1a)
2-(4-Bromophenyl)-1-phenyl-1H-phenanthro[9，10-d]imidazolederivatives(1a)
.mp=255 ℃ of productive rate: 3.88g (90%). δ H(200MHz; CDCl 3Me 4Si) 7.18 (td, J=8.0, J=1.1Hz, 1H), 7.25-7.30 (m, 1H), 7.39-7.56 (m, 7H), 7.58-7.78 (m, 5H), 8.70 (d, J=8.1Hz, 1H), 8.76 (d, J=8.4Hz, 1H), 8.84 (d, J=7.8Hz, 1H); δ C(50MHz; CDCl 3Me 4Si) 120.8 (d), 122.7 (d), 122.9 (s), 123.1 (d), 123.4 (s), 124.1 (d), 125.0 (d), 125.7 (d), 126.3 (d), 127.1 (s), 127.3 (d), 128.3 (s), 129.0 (d), 129.4 (s), 129.5 (s), 130.0 (d), 130.3 (d), 130.8 (d), 131.4 (d), 137.5 (s), 138.6 (s), 149.7 (s) .IR (KBr): 3055,1594,1494,1450em -1.HRMS (EI +) Calc.for C 27H 17BrN 2: 448.0575, Found (M +): 448.0576.
2-(4-bromophenyl)-1-is right-and tolyl-1H-phenanthro-[9,10-d] imidazoles (2-(4-Bromophenyl)-1-p-tolyl-1H-phenanthro[9,10-d] imidazole) (1b)
.mp=236 ℃ of productive rate: 3.91g (88%). δ H(200MHz; CDCl 3Me 4Si) 2.53 (s, 3H), 7.17-7.27 (m, 2H), 7.30-7.53 (m, 9H), 7.58-7.67 (m, 1H), 7.73 (td, J=7.9, J=1.0Hz, 1H), 8.68 (d, J=8.1Hz, 1H), 8.74 (d, J=8.4Hz, 1H), 8.83 (d, J=7.5Hz, lH); δ C(50MHz; CDCl 3Me 4Si) 21.5 (q), 120.8 (d), 122.6 (d), 122.9 (s), 123.1 (d), 123.2 (s), 124.0 (d), 124.9 (d), 125.6 (d), 126.2 (d), 127.1 (s), 127.3 (d), 128.2 (s), 128.3 (s), 128.60 (d), 129.3 (s), 129.5 (s), 130.7 (d), 130.9 (d), 131.4 (d), 135.8 (s), 137.3 (s), 140.1 (s), 149.7 (s) .IR (KBr): 3047,2966,1609,1513,1450,1373cm -1.HRMS (EI +) Calc.for C 28H 19BrN 2: 462.0732, Found (M +): 462.0729.
2-(4-bromophenyl)-1-(4-p-methoxy-phenyl-1H-phenanthro-[9,10-d] imidazoles (2-(4-Bromophenyl)-1-(4-methoxyphenyl)-1H-phenanthro[9,10-d] imidazole) (1c)
.mp=239 ℃ of productive rate: 3.68g (80%). δ H(200MHz; CDCl 3Me 4Si) 3.95 (s, 3H), 7.09 (d, J=8.7Hz, 2H), 7.22-7.34 (m, 1H), 7.39 (d, J=8.7Hz, 2H), 7.44-7.56 (m, 6H), 7.61-7.68 (m, 1H), 7.74 (td, J=8.0, J=1.1Hz, 1H), 8.70 (d, J=7.9Hz, 1H), 8.76 (d, J=8.4Hz, 1H), 8.83 (d, J=8.0Hz, 1H); δ C(50MHz; CDCl 3Me 4Si) 55.6 (q), 115.3 (d), 120.8 (d), 122.6 (d), 123.0 (s), 123.1 (d), 123.3 (s), 124.1 (d), 125.0 (d), 125.6 (d), 126.3 (d), 127.1 (s), 127.3 (d), 128.2 (s), 128.4 (s), 129.3 (s), 129.5 (s), 130.1 (d), 130.8 (d), 130.9 (s), 131.4 (d), 137.3 (s), 149.9 (s), 160.4 (s) .IR (KBr): 3055,2959,1609,1513,1450,1251,1030em -1.HRMS (EI +) Calc.forC 28H 19BrN 2O 478.0681, Found (M +): 478.0681.
Two phenanthro-imidazolyl derivatives 2a-2c's is synthetic
Have in the round bottom beaker compound 1a (2.0g, 4.45mmol), NiCl 2(0.058g, 0.45mmol), zinc powder (0.29g, 4.45mmol), KI (1.11g, 6.68mmol), PPh 3(0.47g 1.78mmol), uses nitrogen purging three times, and (N, N-dimethylformamide DMF), stir this mixture 24 hours in nitrogen environment under 80 ℃ to add the 20mL dimethyl formamide subsequently.Then, thermal reaction mixture is filtered, removing zinc and inorganic salt, and with rest solution CH 2Cl 2Clean.In vacuum environment, evapotranspire to leaching solution, afterwards residue is collected, and with washed with methanol and with vacuum-drying to obtain product 2a (1.35g, 82%).Again by the vacuum-sublimation technology, with 330 ℃ and 3～5 * 10 -3Pa is further purified product.Other derivative 2b can be produced according to similar step preparation with 1c by compound 1b respectively with 2c.The synthesis path that in Fig. 1, has shown two phenanthro-imidazolyl derivatives.Below show productive rate and relevant spectroscopic data.
4,4 '-two (biphenyl of 1-phenyl-1H-phenanthro-[9,10-d] imidazoles-2yl) (4,4 '-Bis (1-phenyl-1H-phenanthro[9,10-d] imidazole-2yl)-biphenyl, PPIP) 2a
.mp.=402 ℃ of productive rate: 1.35g (82%). δ H(200MHz; CDCl 3Me 4Si) 6.73-7.79 (m, 28H), 8.72 (d, J=8.0Hz, 2H), 8.79 (d, J=8.4Hz, 2H), 8.89 (d, J=7.9Hz, 2H) .IR (KBr): 3055,1595,1494,1451cm -1.HRMS (FAB +) Calc.for C 54H 34N 4738.2783, Found (MH +) 739.2861Anal.Calc.forC 54H 34N 4: C, 87.78; H, 4.64; N, 7.58.Found:C, 87.67; H, 4.68; N, 7.52.
4,4 '-two (1-is right-biphenyl of tolyl-1H-phenanthro-[9,10-d] imidazoles-2yl) (4,4 '-Bis (1-p-tolyl-1H-phenanthro[9,10-d] imidazole-2yl)-biphenyl, TPIP), 2b
.mp.=405 ℃ of productive rate: 1.37g (80%). δ H(200MHz; CDCl 3Me 4Si) 2.57 (s, 6H), 7.16-7.79 (m, 26H), 8.72 (d, J=8.0Hz, 2H), 8.78 (d, J=8.4Hz, 2H), 8.88 (d, J=7.9Hz, 2H) .IR (KBr): 3055,2915,1605,1513,1450,1376cm -1.HRMS (FAB +) Calc.for C 56H 38N 4: 766.3096, Found (MH +) 767.3177.Anal.Calc.for C 56H 38N 4: C, 87.70; H, 4.99; N, 7.31.Found:C, 87.71; H, 5.01; N, 7.34.
4,4 '-two (1-(biphenyl of 4-p-methoxy-phenyl-1H-phenanthro-[9,10-d] imidazoles-2yl) (4,4 '-Bis (1-(4-methoxyphenyl)-1H-phenanthro[9,10-d] imidazole-2yl)-biphenyl, MPIP) 2c
.mp.=403 ℃ of productive rate: 1.34g (75%). δ H(200MHz; CDCl 3Me 4Si) 3.98 (s, 6H), 6.73-7.79 (m, 26H), 8.72 (d, J=8.3Hz, 2H), 8.78 (d, J=8.2Hz, 2H), 8.88 (d, J=8.3Hz, 2H) .IR (KBr): 3062,2959,1601,1509,1458,1249,1031cm -1.HRMS (FAB +) Calc.for C 56H 38N 4O 2: 798.2995, Found (MH +) 799.3073.Anal.Calcd for C 56H 38N 4O 2: C, 84.19; H, 4.79; N, 7.01.Found:C, 84.18; H, 4.74; N, 7.03.
Therefore, those skilled in the art by selecting the combination of different starting raw material with different intermediate products, just can form various compound among the present invention as can be known.For example, p-bromobenzaldehyde can be replaced by the substituent p-bromobenzaldehyde of tool, and the substituent aniline of tool can be replaced by 4-aminopyridine.
In addition, what should indicate is that the synthetic of two phenanthro-imidazolyl derivatives can be reached via simple two steps by commercially available starting raw material, and does not need expensive precious metal catalyst thing.In addition, above-mentioned preparation process is suitable for mass production, because need not carry out the chromatography purification step in building-up process.
As shown in table 1, these compounds represent relatively more excellent thermal properties, and it has higher glass transition temperature (197～200C), and the blue light of concentrating with the emission spike emission of 462～466nm.
The physical properties of table 1. pair phenanthro-imidazole-based compounds
Figure GSA00000056298200091
A. measure gained by DSC; ND: do not measure (not detected)
B. with dilution CH 2Cl 2Solution (＜10 -5M) record
C. with dilution CH 2Cl 2Solution (＜10 -5M) measure, and with 2-aminopyridine (2-aminopyridine) (＜10 -5M) as reference value
As aforementioned, A3 can be polycyclic aromatic hydrocarbons, therefore, and the group that the optional free naphthalene of A3 (naphthalene), anthracene (anthracene), luxuriant and rich with fragrance (phenanthrene), (chrysene) in the wrong and pyrene (pyrene) are formed.Fig. 2 is the synoptic diagram that shows the building-up process of two phenanthro-imdazole derivatives, and wherein A3 is naphthalene or anthracene.
As previously mentioned, Xin Ying two phenanthro-imidazole-based compounds can be used for preparing luminescent layer and/or as electron transfer layer.Therefore, comprise according to a kind of el light emitting device of one embodiment of the invention: a negative electrode, an anode and be arranged at negative electrode and anode between an organic layer, wherein organic layer comprises above-mentioned two phenanthro-imidazole-based compounds.Organic layer can be as luminescent layer, and two phenanthro-imidazole-based compounds can be as main body luminescent material or object luminescent material; It is luminous also can to carry out doping way; In addition, organic layer also can be as electron transfer layer, and two phenanthro-imidazole-based compounds can be as main or accessory electron transport material.Therefore, above-mentioned organic layer can be as luminescent layer and/or electron transfer layer to form above-mentioned el light emitting device.
This el light emitting device also can comprise hole transmission layer and/or electron transfer layer.Hole transmission layer can comprise 4,4 '-two [N-(1-naphthyl)-N-phenylamino] biphenyl (4,4 '-bis[N-(1-naphthyl)-N-phenylamino] biphenyl, NPB), N, two toluene nitrogen-N of N-, N ' phenylbenzene-1,1 '-biphenyl-4,4 '-diamines (N, N '-di-m-tolyl-N, N '-diphenyl-1,1 '-biphenyl-4,4 ' diamine, TPD) or 4,4 ', 4 " three (N-carbazole) triphenylamine (4; 4 ', 4 " tris (N-carbazolyl) triphenyl amine, TCTA).
Electron transfer layer can comprise: metal chelate, 1,3,4-oxadiazoles (1,3,4-oxadiazole) or 1,2,4-triazole (1,2,4-triazole) or derivatives thereof, thiapyran sulfone (thiopyran sulfone) or derivatives thereof or two (the two methane amides (bis (benzimidazolyl) perylenedicarboximid) of benzimidazolyl-) perylene.
Figure GSA00000056298200111
El light emitting device also can comprise luminescent layer.Luminescent layer can comprise host emitter (hostemitter), for example: and 9,10-two (anthracene of naphthalene-2-yl) ( 9,10-Di (naphth-2-yl) anthraceneADN), 1-(4-(1-pyrene) phenyl) pyrene (1-(4-(1-pyrenyl) phenyl) pyrene, PPP), 1-(2,5-dimethoxy-4 '-(1-pyrene) phenyl) (1-(2 for pyrene, 5-dimethoxy-4-(1-pyrenyl)-phenyl) pyrene, DOPPP), 1-(2,5-dimethyl-4-(1-pyrene) phenyl) (1-(2 for pyrene, 5-dimethyl-4-(1-pyrenyl) phenyl) pyrene, DMPPP), 4,4 '-N, N '-two carbazole-biphenyl (4,4 '-N, N '-dicarbazole-biphenyl, CBP), 1, two (9-carbazole) benzene (1 of 3-, 3-bis (9-carbazolyl) benzene, mCP) or p-two (triphenyl is silica-based) benzene (p-bis (triphenylsilyly) benzene, UGH2); Or guest emitter (guestemitter), comprising: two (3,5-fluoro-2-(2-pyridyl) phenyl-(2-carboxyl pyridine base) iridium (III) ( Bis (3,5-Difluoro-2-(2-pyridyl) phenyl-(2-carboxypyridyl) iridium (III), FIrPic), three (2-phenylpyridine) iridium (III) ( Tris (2-phenylpyridine) iridium (III),(IrPPy) 3) or 4,4 '-two [2-14-(N, N-hexichol amido) phenyl] vinyl) biphenyl (4,4 '-bis[2-14-(N, N-diphenylamino) phenyl] vinyl) biphenyl, DPAVBi).
Figure GSA00000056298200121
Host emitter
Figure GSA00000056298200122
Guest emitter
The preparation example of el light emitting device is disclosed below.The preparation of this el light emitting device can be by less than 5 * 10 -6Under the pressure condition of Torr, the material vacuum moulding machine extremely is coated with the indium tin oxide that one deck electrical sheet resistance value is 25ohm/square (indium tin oxide, clean glass ITO) in advance.The sedimentation rate of organic compound is
Figure GSA00000056298200131
The formation of negative electrode deposits LiF (1.0nm) by priority and Al (100nm) finishes, and its sedimentation rate is respectively 0.1 and reaches
Figure GSA00000056298200132
Figure GSA00000056298200133
The effective area of photodiode is 9.00mm 2
Have saturated blue light and high T owing to find two phenanthro-imidazolyl derivatives g, so it can be as the blue light host emitter in the Organic Light Emitting Diode.The structure of blue light electroluminescent cell comprises: ITO/ hole transmission layer (hole-transporting layer, HTL) (50nm)/PPIP (30nm)/2,9-dimethyl-4,7-phenylbenzene-1, and the 10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, BCP) (15nm)/three (oxine) aluminium (tris (8-hydroxyquinolinato) aluminum, Alq 3) (50nm)/LiF (1nm)/Al (100nm).Wherein use three kinds of different HTL to survey the electroluminescent character of two phenanthro-imidazole-based compounds, comprise: 4,4 '-two [N-(1-naphthyl)-N-phenylamino] biphenyl (4,4 '-bis[N-(1-naphthyl)-N-phenylamino] biphenyl, NPB), N, two toluene nitrogen-N of N-, N '-phenylbenzene-1,1 '-biphenyl-4,4 '-diamines (N, N '-di-m-tolyl-N, N '-diphenyl-1,1 '-biphenyl-4,4 ' diamine, TPD) or 4,4 ', 4 " three (N-carbazole) triphenylamine (4,4 '; 4 "-tris (N-carbazolyl) triphenyl amine, TCTA).(therefore photoluminescence, PL) efficient are further elected as host emitter because PPIP has higher photoluminescence.
Table 2 display element structure and effect thereof, and Fig. 3 shows the energy rank and the chemical structure of organic materials.Can know by Fig. 4 and table 2 and to learn, these three kinds with two phenanthro-imidazole-based compounds element that is twinkler can be quite low voltage (≤4.1V) start, and when 12～15V, reach high-high brightness.Fig. 5 shows the EL spectrum of generation, and its PL spectrum to above-mentioned solid-state PPIP is similar.These three kinds of devices all send ethereal blue light (CIE y≤ 0.15), and these numerical value and the American National TV council (National Television Standards Committee, the blue light video signal display standard of NTSC) being advised is quite approaching.In addition, these devices with two phenanthro-imidazole-based compounds also show stable EL spectrum under the voltage that applies the broad interval.B is an example with device, and when voltage was increased to the required voltage of high-high brightness by 6V, its EL spectrum did not change, as shown in Figure 6.
The usefulness that table 2. is the Organic Light Emitting Diode of twinkler with two phenanthro-imidazole-based compounds a
aL: brightness, η Ext: external quantum efficiency (external quantum efficiency), η c: current efficiency (current efficiency), and η p: electric energy efficiency (power efficiency) is the maximum value of el light emitting device.
bApparatus structure: ITO/HTL (50nm)/(PPIP, TPIP or APIP) (30nm)/BCP (15nm)/Alq (30nm)/LiF (1nm)/Al (100nm)
cV On: it is 1cd/m that trigger voltage is defined as brightness 2Required voltage.
For understanding two phenanthro-imidazole-based compounds more is the EL character of the element of twinkler, the present invention measures the highest electronics by absorption spectrum (the minimum energy absorption edge by UV-light-visible absorption spectrum is calculated) and cyclic voltammogram and occupies orbital (highest occupied molecularorbital, HOMO), minimum electronics does not occupy orbital (lowest unoccupied molecularorbital, LUMO) energy rank.The HOMO/LUMO of PPIP can rank be 2.8/5.7eV.Host emitter has low LUMO energy rank, and it is similar with the standard electronic transport material TPBI (1,3,5-tris (N-phenylbenzimidizol-2-yl) benzene) that with the imidazoles is substrate.According to energy level diagram shown in Figure 3, electronics can overcome the PPIP layer and as the less injection energy barrier (0.2eV) between the BCP layer of electric transmission and hole barrier layer, and then successfully enters the PPIP layer.On the other hand, the hole between PPIP and the three kinds of different HTL inject energy barrier also be quite little (＜0.3eV).The injection energy barrier of charged particle carrier is less may to be the reason that causes relatively low cut-in voltage.
As table 2 and shown in Figure 7, the element that is twinkler with two phenanthro-imidazole-based compounds presents higher EL efficient.These the maximum external quantum efficiencies that had of device and current efficiency are respectively 4.77～6.31% and 5.92～7.47cd/A.Among these devices, use TCTA can reach the ethereal blue light of full blast as the resulting device of HTL C.This possibility of result is because have than equilibrated charge transfer character in the emission layer, and it is that more excellent electric charge injects and limitation is reached because TCTA HTL has.Except realizing high η ExtAnd η cOutside the value, with PPIP be the device of substrate also keep quite high electric energy efficiency (4.69～7.30lm/W) because they have lower driving voltage.The not doping type OLED that has high external quantum efficiency and good colour purity at present, its corresponding on-peak electric energy efficient still lower comparatively speaking (＜4.5lm/W).As shown in Figure 7, at 200cd/m 2Practical brightness under, the electric energy efficiency of device C still can maintain the high standard of about 5lm/W.
Comprehensively above-mentioned, but the invention provides a kind of transmission electronic and electroluminescent compound.These materials present more excellent thermal properties, and it has higher glass transition temperature (about 200 ℃) and efficient blue light (about 465nm) emission.
The present invention also provides a kind of el light emitting device, its have lower trigger voltage (＜3V) and ethereal blue light (CIE with good color purity y≤ 0.15).Wherein preferred device has been realized higher electric energy efficiency (7.30lm/W).In addition, even if the efficient of this device is increased to 200cd/m with brightness 2Below still can maintain high level (5lm/W).
Above-described embodiment only is for technological thought of the present invention and characteristics are described, its purpose makes those skilled in the art can understand content of the present invention and is implementing according to this, and can not limit the present invention with this, be that every equalization of doing according to spirit disclosed in this invention changes or modifies, must be encompassed in the claim of the present invention institute restricted portion.

Claims (17)

1. two phenanthro-imidazole-based compounds, it comprises following chemical formula:
Figure FSA00000056298100011
Wherein, A1 and A2 comprise identical or different aromatic nucleus, and A3 comprises a polycyclic aromatic hydrocarbons or at least two aromatic series bases, and each carbon atom of A1 to A3 and phenanthro-base can have or not have substituting group independently.
2. as claimed in claim 1 pair of phenanthro-imidazole-based compounds, wherein a substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises a halogen atom, one C1～C20 alkyl chain, one C1～C20 oxyalkyl chain, one C1～C20 alkylhalide group chain, one C1～C20 halogen oxyalkyl chain, a carbonyl, a cyano group or a nitro.
3. as claimed in claim 1 pair of phenanthro-imidazole-based compounds, wherein A3 comprises two aromatic series base A4 and A5, and each carbon atom of A4 and A5 can have or not have substituting group independently.
Figure FSA00000056298100012
4. as claimed in claim 3 pair of phenanthro-imidazole-based compounds, wherein A4 and A5 are phenyl ring.
5. as claimed in claim 1 pair of phenanthro-imidazole-based compounds, wherein A3 is selected from the group that is made up of naphthalene, anthracene, phenanthrene, (chrysene) in the wrong and pyrene.
6. as claimed in claim 1 pair of phenanthro-imidazole-based compounds, wherein A1 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
7. as claimed in claim 1 pair of phenanthro-imidazole-based compounds, wherein A2 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
8. el light emitting device comprises:
One negative electrode;
One anode; And
One organic layer is arranged between this negative electrode and this anode, and wherein this organic layer comprises two phenanthro-imidazole-based compounds, and this pair phenanthro-imidazole-based compounds comprises following chemical formula:
Figure FSA00000056298100021
Wherein, A1 and A2 comprise identical or different aromatic nucleus, and A3 comprises a polycyclic aromatic hydrocarbons or at least two aromatic series bases, and each carbon atom of A1 to A3 and phenanthro-base can have or not have substituting group independently;
One substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises a halogen atom, one C1～C20 alkyl chain, one C1～C20 oxyalkyl chain, one C1～C20 alkylhalide group chain, one C1～C20 halogen oxyalkyl chain, a carbonyl, a cyano group or a nitro;
9. el light emitting device as claimed in claim 8, wherein a substituting group of each carbon atom of A1 to A3 and phenanthro-base optionally comprises a halogen atom, one C1～C20 alkyl chain, one C1～C20 oxyalkyl chain, one C1～C20 alkylhalide group chain, one C1～C20 halogen oxyalkyl chain, a carbonyl, a cyano group or a nitro.
10. el light emitting device as claimed in claim 8, wherein A3 comprises two aromatic series base A4 and A5, and each carbon atom of A4 and A5 can have or not have substituting group independently.
Figure FSA00000056298100031
11. as claimed in claim 10 pair of phenanthro-imidazole-based compounds, wherein A4 and A5 are phenyl ring.
12. el light emitting device as claimed in claim 8, wherein A3 is selected from the group that is made up of naphthalene, anthracene, phenanthrene, (chrysene) in the wrong and pyrene.
13. el light emitting device as claimed in claim 8, wherein A1 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
14. el light emitting device as claimed in claim 8, wherein A2 is selected from the group that is made up of the phenyl ring of not replacement, methyl substituted and methoxyl group replacement.
15. el light emitting device as claimed in claim 8, wherein said organic layer is a luminescent layer, and described pair of phenanthro-imidazole-based compounds is a main body luminescent material.
16. el light emitting device as claimed in claim 8, wherein said organic layer is a luminescent layer, and described pair of phenanthro-imidazole-based compounds is an object luminescent material.
17. el light emitting device as claimed in claim 8, wherein said organic layer is an electron transfer layer, and described pair of phenanthro-imidazole-based compounds is an electron transport material.
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